NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	680.2
Volume:	633.575
LogP:	0.163
LogD:	-0.075
LogS:	-3.169
# Rotatable Bonds:	13
TPSA:	271.59
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.091
Synthetic Accessibility Score:	4.777
Fsp3:	0.419
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.471
MDCK Permeability:	6.470926746260375e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.952
20% Bioavailability (F20%):	0.487
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	92.59635162353516%
Volume Distribution (VD):	0.438
Pgp-substrate:	9.14803409576416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.743
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	1.287
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.94
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.007

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476865

Natural Product ID:	NPC476865
*Common Name:**	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoate
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	GESDPGMCBUDDMA-NSWVMONVSA-N
Standard InCHI:	InChI=1S/C31H36O17/c1-43-19-11-15(2-6-16(19)33)4-8-22(35)44-13-21-25(38)27(40)28(41)30(47-21)45-18-7-3-14(10-17(18)34)5-9-23(36)48-31-29(42)26(39)24(37)20(12-32)46-31/h2-11,20-21,24-34,37-42H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24-,25-,26+,27+,28-,29-,30-,31+/m1/s1
SMILES:	COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C(C=C3)/C=C/C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33548	Clematis tashiroi	Species	Ranunculaceae	Eukaryota	aerial parts	Heping District, Taichung City, Taiwan	2012-AUG	PMID[26143931]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		ED50	=	87	nM	PMID[26143931]
NPT1	Others	Radical scavenging activity		Activity	=	74.8	%	PMID[26143931]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476865 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	1571
0.2-0.3	4053
0.3-0.4	9561
0.4-0.5	8647
0.5-0.6	5899
0.6-0.7	8122
0.7-0.8	3800
0.8-0.85	447
0.85-0.9	180
0.9-0.95	71
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC476868
0.9928	High Similarity	NPC476864
0.9928	High Similarity	NPC476866
0.9928	High Similarity	NPC476869
0.9855	High Similarity	NPC476867
0.971	High Similarity	NPC157816
0.9643	High Similarity	NPC34927
0.9643	High Similarity	NPC100998
0.9643	High Similarity	NPC34587
0.9643	High Similarity	NPC252292
0.9643	High Similarity	NPC476382
0.964	High Similarity	NPC478239
0.958	High Similarity	NPC476871
0.9565	High Similarity	NPC202700
0.951	High Similarity	NPC476386
0.951	High Similarity	NPC306890
0.951	High Similarity	NPC473427
0.951	High Similarity	NPC470933
0.951	High Similarity	NPC476398
0.951	High Similarity	NPC94871
0.951	High Similarity	NPC259347
0.951	High Similarity	NPC471062
0.9507	High Similarity	NPC232992
0.9504	High Similarity	NPC83743
0.9504	High Similarity	NPC262182
0.9504	High Similarity	NPC287615
0.9504	High Similarity	NPC216819
0.9496	High Similarity	NPC186406
0.9493	High Similarity	NPC100389
0.9444	High Similarity	NPC188393
0.9444	High Similarity	NPC470927
0.9444	High Similarity	NPC257970
0.9444	High Similarity	NPC470934
0.9441	High Similarity	NPC300262
0.9441	High Similarity	NPC201148
0.9441	High Similarity	NPC210611
0.9441	High Similarity	NPC199311
0.9441	High Similarity	NPC28651
0.9441	High Similarity	NPC3460
0.9441	High Similarity	NPC215095
0.9441	High Similarity	NPC261122
0.9441	High Similarity	NPC192763
0.9441	High Similarity	NPC80732
0.9437	High Similarity	NPC199928
0.9433	High Similarity	NPC110063
0.9433	High Similarity	NPC232228
0.9429	High Similarity	NPC140502
0.9375	High Similarity	NPC106138
0.9357	High Similarity	NPC134405
0.9357	High Similarity	NPC476385
0.9348	High Similarity	NPC186418
0.9348	High Similarity	NPC37468
0.9348	High Similarity	NPC157554
0.9306	High Similarity	NPC478237
0.9296	High Similarity	NPC292443
0.9247	High Similarity	NPC85192
0.9247	High Similarity	NPC143480
0.9247	High Similarity	NPC125823
0.9247	High Similarity	NPC7145
0.9241	High Similarity	NPC283839
0.9241	High Similarity	NPC90896
0.922	High Similarity	NPC47471
0.922	High Similarity	NPC476377
0.9214	High Similarity	NPC197316
0.9214	High Similarity	NPC81515
0.9214	High Similarity	NPC68092
0.9214	High Similarity	NPC226005
0.9214	High Similarity	NPC472350
0.9214	High Similarity	NPC89105
0.9214	High Similarity	NPC64141
0.9214	High Similarity	NPC205195
0.9214	High Similarity	NPC476383
0.9184	High Similarity	NPC289967
0.9184	High Similarity	NPC472611
0.9184	High Similarity	NPC472612
0.9155	High Similarity	NPC473792
0.9155	High Similarity	NPC473873
0.9155	High Similarity	NPC265648
0.9155	High Similarity	NPC222433
0.9149	High Similarity	NPC473799
0.9149	High Similarity	NPC106944
0.9149	High Similarity	NPC475530
0.9143	High Similarity	NPC78363
0.9143	High Similarity	NPC470413
0.9143	High Similarity	NPC260425
0.9143	High Similarity	NPC126206
0.9143	High Similarity	NPC138738
0.9143	High Similarity	NPC476376
0.9137	High Similarity	NPC476870
0.9091	High Similarity	NPC476381
0.9091	High Similarity	NPC269141
0.9091	High Similarity	NPC476384
0.9091	High Similarity	NPC247032
0.9091	High Similarity	NPC298257
0.9091	High Similarity	NPC96795
0.9091	High Similarity	NPC476397
0.9091	High Similarity	NPC476375
0.9091	High Similarity	NPC476378
0.9091	High Similarity	NPC205864
0.9091	High Similarity	NPC76406
0.9091	High Similarity	NPC119537
0.9091	High Similarity	NPC264632
0.9091	High Similarity	NPC112
0.9091	High Similarity	NPC476380
0.9091	High Similarity	NPC175214
0.9071	High Similarity	NPC471664
0.9071	High Similarity	NPC471665
0.9067	High Similarity	NPC11411
0.9058	High Similarity	NPC473285
0.9054	High Similarity	NPC478268
0.9028	High Similarity	NPC141455
0.9028	High Similarity	NPC296954
0.9028	High Similarity	NPC297342
0.9028	High Similarity	NPC64195
0.9028	High Similarity	NPC196063
0.9028	High Similarity	NPC300894
0.9	High Similarity	NPC55040
0.8993	High Similarity	NPC150442
0.898	High Similarity	NPC111785
0.898	High Similarity	NPC478242
0.8966	High Similarity	NPC274960
0.8966	High Similarity	NPC473909
0.8966	High Similarity	NPC143120
0.8958	High Similarity	NPC113680
0.8958	High Similarity	NPC278961
0.8958	High Similarity	NPC105005
0.8954	High Similarity	NPC149873
0.8954	High Similarity	NPC7191
0.8947	High Similarity	NPC478269
0.8944	High Similarity	NPC98777
0.8944	High Similarity	NPC212770
0.8936	High Similarity	NPC177035
0.8936	High Similarity	NPC52277
0.8936	High Similarity	NPC199459
0.8933	High Similarity	NPC327032
0.8933	High Similarity	NPC191046
0.8933	High Similarity	NPC194095
0.8929	High Similarity	NPC287597
0.8929	High Similarity	NPC135127
0.8929	High Similarity	NPC34293
0.8929	High Similarity	NPC886
0.8929	High Similarity	NPC187194
0.8929	High Similarity	NPC35731
0.8929	High Similarity	NPC471883
0.8926	High Similarity	NPC215060
0.8926	High Similarity	NPC169404
0.8926	High Similarity	NPC476352
0.8926	High Similarity	NPC176186
0.8926	High Similarity	NPC53587
0.8912	High Similarity	NPC116229
0.8912	High Similarity	NPC93924
0.8904	High Similarity	NPC229505
0.8889	High Similarity	NPC469559
0.8889	High Similarity	NPC145319
0.8882	High Similarity	NPC133984
0.8873	High Similarity	NPC59324
0.8873	High Similarity	NPC65530
0.8873	High Similarity	NPC124149
0.8867	High Similarity	NPC246893
0.8867	High Similarity	NPC157898
0.8859	High Similarity	NPC213197
0.8849	High Similarity	NPC246869
0.8849	High Similarity	NPC225384
0.8849	High Similarity	NPC138777
0.8844	High Similarity	NPC52740
0.8844	High Similarity	NPC41844
0.8841	High Similarity	NPC229784
0.8841	High Similarity	NPC477294
0.8841	High Similarity	NPC307110
0.8841	High Similarity	NPC477293
0.8841	High Similarity	NPC248355
0.8836	High Similarity	NPC138915
0.8831	High Similarity	NPC478267
0.8828	High Similarity	NPC46092
0.8828	High Similarity	NPC470950
0.8828	High Similarity	NPC185307
0.8816	High Similarity	NPC471405
0.8816	High Similarity	NPC228357
0.8816	High Similarity	NPC478266
0.8811	High Similarity	NPC321638
0.8811	High Similarity	NPC328273
0.8811	High Similarity	NPC171134
0.8811	High Similarity	NPC321184
0.8803	High Similarity	NPC166180
0.8803	High Similarity	NPC164857
0.8803	High Similarity	NPC203230
0.8803	High Similarity	NPC197723
0.8803	High Similarity	NPC3293
0.8803	High Similarity	NPC242028
0.8803	High Similarity	NPC138350
0.8803	High Similarity	NPC40664
0.8803	High Similarity	NPC165482
0.88	High Similarity	NPC134905
0.88	High Similarity	NPC36130
0.8794	High Similarity	NPC476411
0.8792	High Similarity	NPC475224
0.8792	High Similarity	NPC114740
0.8784	High Similarity	NPC476348
0.8784	High Similarity	NPC187398
0.8776	High Similarity	NPC125755

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476865 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	859
0.2-0.3	1819
0.3-0.4	2901
0.4-0.5	1808
0.5-0.6	994
0.6-0.7	439
0.7-0.8	52
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9214	High Similarity	NPD7266	Discontinued
0.8725	High Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD7472	Approved
0.8272	Intermediate Similarity	NPD7054	Approved
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8121	Intermediate Similarity	NPD7685	Pre-registration
0.8072	Intermediate Similarity	NPD7808	Phase 3
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD7228	Approved
0.7964	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3027	Phase 3
0.7891	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1613	Approved
0.7887	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD8455	Phase 2
0.7829	Intermediate Similarity	NPD6674	Discontinued
0.7746	Intermediate Similarity	NPD1091	Approved
0.7742	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6190	Approved
0.7716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6234	Discontinued
0.7651	Intermediate Similarity	NPD6166	Phase 2
0.7651	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8312	Approved
0.7602	Intermediate Similarity	NPD8313	Approved
0.7588	Intermediate Similarity	NPD7240	Approved
0.7578	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD1934	Approved
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4967	Phase 2
0.7546	Intermediate Similarity	NPD4966	Approved
0.7546	Intermediate Similarity	NPD4965	Approved
0.7535	Intermediate Similarity	NPD1357	Approved
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7412	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD5536	Phase 2
0.7386	Intermediate Similarity	NPD7097	Phase 1
0.7379	Intermediate Similarity	NPD3705	Approved
0.7378	Intermediate Similarity	NPD3817	Phase 2
0.7375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8127	Discontinued
0.7317	Intermediate Similarity	NPD2801	Approved
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD7075	Discontinued
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7255	Intermediate Similarity	NPD1933	Approved
0.7255	Intermediate Similarity	NPD4340	Discontinued
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7233	Intermediate Similarity	NPD5058	Phase 3
0.7229	Intermediate Similarity	NPD3882	Suspended
0.7219	Intermediate Similarity	NPD7095	Approved
0.7214	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7174	Intermediate Similarity	NPD1358	Approved
0.7169	Intermediate Similarity	NPD5402	Approved
0.7162	Intermediate Similarity	NPD2983	Phase 2
0.7162	Intermediate Similarity	NPD2982	Phase 2
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7117	Intermediate Similarity	NPD3687	Approved
0.7117	Intermediate Similarity	NPD3686	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2977	Approved
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2978	Approved
0.7097	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7095	Intermediate Similarity	NPD2981	Phase 2
0.7086	Intermediate Similarity	NPD9494	Approved
0.7081	Intermediate Similarity	NPD1511	Approved
0.7078	Intermediate Similarity	NPD1558	Phase 1
0.7075	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD5403	Approved
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7051	Intermediate Similarity	NPD4538	Approved
0.7051	Intermediate Similarity	NPD4536	Approved
0.7051	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7549	Discontinued
0.7044	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7843	Approved
0.7039	Intermediate Similarity	NPD6841	Approved
0.7039	Intermediate Similarity	NPD6842	Approved
0.7039	Intermediate Similarity	NPD6843	Phase 3
0.7032	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD447	Suspended
0.7027	Intermediate Similarity	NPD422	Phase 1
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7014	Intermediate Similarity	NPD7157	Approved
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5494	Approved
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6994	Remote Similarity	NPD1512	Approved
0.6994	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5283	Phase 1
0.6989	Remote Similarity	NPD7038	Approved
0.6989	Remote Similarity	NPD7039	Approved
0.6978	Remote Similarity	NPD3134	Approved
0.6975	Remote Similarity	NPD4357	Discontinued
0.6974	Remote Similarity	NPD3018	Phase 2
0.6968	Remote Similarity	NPD3620	Phase 2
0.6968	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6801	Discontinued
0.6946	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5401	Approved
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5535	Approved
0.6919	Remote Similarity	NPD6232	Discontinued
0.6919	Remote Similarity	NPD3787	Discontinued
0.6913	Remote Similarity	NPD1610	Phase 2
0.6903	Remote Similarity	NPD4062	Phase 3
0.6899	Remote Similarity	NPD7033	Discontinued
0.6899	Remote Similarity	NPD5960	Phase 3
0.6899	Remote Similarity	NPD5588	Approved
0.6897	Remote Similarity	NPD7473	Discontinued
0.6894	Remote Similarity	NPD3750	Approved
0.6894	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6386	Approved
0.6886	Remote Similarity	NPD7411	Suspended
0.6886	Remote Similarity	NPD6385	Approved
0.6879	Remote Similarity	NPD2684	Approved
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6799	Approved
0.6871	Remote Similarity	NPD1548	Phase 1
0.6867	Remote Similarity	NPD7458	Discontinued
0.6859	Remote Similarity	NPD4140	Approved
0.6855	Remote Similarity	NPD2935	Discontinued
0.6835	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3060	Approved
0.6829	Remote Similarity	NPD4123	Phase 3
0.6829	Remote Similarity	NPD3536	Discontinued
0.6824	Remote Similarity	NPD7768	Phase 2
0.6824	Remote Similarity	NPD5585	Approved
0.6823	Remote Similarity	NPD8151	Discontinued
0.6813	Remote Similarity	NPD1375	Discontinued
0.6812	Remote Similarity	NPD291	Approved
0.6809	Remote Similarity	NPD290	Approved
0.6788	Remote Similarity	NPD6273	Approved
0.6784	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6671	Approved
0.6779	Remote Similarity	NPD1778	Approved
0.6776	Remote Similarity	NPD8651	Approved
0.6772	Remote Similarity	NPD2492	Phase 1
0.677	Remote Similarity	NPD2424	Discontinued
0.677	Remote Similarity	NPD1549	Phase 2
0.6766	Remote Similarity	NPD3455	Phase 2
0.6766	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5353	Approved
0.6755	Remote Similarity	NPD1608	Approved
0.6753	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7783	Phase 2
0.675	Remote Similarity	NPD1551	Phase 2
0.675	Remote Similarity	NPD6032	Approved
0.6747	Remote Similarity	NPD2122	Discontinued
0.6738	Remote Similarity	NPD968	Approved
0.6737	Remote Similarity	NPD7435	Discontinued
0.6732	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4237	Approved
0.6728	Remote Similarity	NPD4236	Phase 3
0.6728	Remote Similarity	NPD4162	Approved
0.6726	Remote Similarity	NPD4678	Approved
0.6726	Remote Similarity	NPD7028	Phase 2
0.6726	Remote Similarity	NPD4675	Approved
0.6713	Remote Similarity	NPD3021	Approved
0.6713	Remote Similarity	NPD556	Approved
0.6713	Remote Similarity	NPD3022	Approved
0.671	Remote Similarity	NPD6832	Phase 2
0.671	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5735	Approved
0.6708	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5563	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data